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Things To Do > Explore a Water Trail > Mathews-Piankatank

Osprey - image courtesy Middleton Evans
Scenic creeks and rivers that make up the Mathews Blueways Water Trails are home to osprey and other wildlife to delight today’s travelers.

Perched on the eastern end of Virginia’s Middle Peninsula, Mathews County is defined by the waters that nearly enclose it—the serpentine Piankatank River to the north, the vast Chesapeake Bay to the east, and the sheltering rivers and coves of Mobjack Bay to the south. Once the domain of Mathews-built sailing ships and traditional wooden fishing boats, these waterways now see more pleasure craft than working vessels. They offer paddlers, bird-watchers, bicyclists, and other outdoor enthusiasts more than 200 miles of shoreline to explore—all reached by scenic networks of water trails, bike routes, and rural highways.

As Captain John Smith and his crew sailed along the Bay’s western shore during their second exploratory voyage in 1608, they traveled and anchored in the waters off what is now Mathews County. Returning to Jamestown late that summer, Smith and his crew mapped the Piankatank River up to its headwaters, stopping at a Piankatank town whose residents, like those of other towns in the region, agreed to share a portion of their corn harvest with the English. According to one account, the paramount chief Powhatan later arranged an ambush in which all of the Piankatank were killed or captured. They were succeeded by another tribe, the Kiskiak, who settled along the Piankatank’s southern shore by the mid-1600s.

Boaters can retrace Smith’s voyage quite a distance up the Piankatank River, but you will need a canoe or kayak to probe its mystical hidden headwaters, Dragon Run. This brackish stream remains one of Virginia’s most unspoiled places, a haven even Smith might recognize today. But the area also attests to the dramatic changes nature has wrought over the centuries. Appreciate them for yourself at New Point Comfort, Mathews County’s rugged southeastern tip, where erosion has sculpted a solitary island crowned by a historic Bay lighthouse. 

Suggested Itinerary: Paddling the Piankatank

Piankatank River Map
A map of the Piankatank River Trail, one of the Mathews Blueways Water Trails is available from the Mathews County Visitor and Information Center. Download a copy of this map.

This tour, best experienced by water, features two stretches of the Piankatank River explored by Captain Smith—the wooded, lightly developed lower river, and the river’s pristine headwaters, Dragon Run.

Route of Discovery

After anchoring inside the mouth of the Piankatank (possibly in Fishing Bay), Smith and his men traveled the length of this comparatively short, winding river in a few days during the late summer of 1608. Kayakers following the Piankatank River Trail, part of the Mathews Blueways Water Trail can retrace the lower portion of Smith’s expedition between still-undeveloped Berkley Island and Queens Creek, a tributary near the river’s mouth whose banks are dotted with houses and cottages. Obtain copies of this and other Blueways’ water trails at the Mathews County Visitor & Information Center in nearby Mathews.

Getting There

Six launch sites are located along the Piankatank River Trail. (Sea and touring kayaks are recommended for most Blueways trails, which feature many stretches of open water.)

What You’ll See

The main Piankatank trail is nearly 12 miles long with five scenic creeks offering additional opportunities for diversion. Along the main route, you’ll see imposing old houses and historic estates as you hug the southern shore. You may glimpse bald eagles, ospreys, and great blue herons, although the river no longer sustains the natural diversity it did in Smith’s day. In recent years, the Piankatank has become a laboratory for an experimental effort to restore one depleted resource, Virginia’s now-decimated oyster population. On several protected reefs here, scientists, like nervous parents, are monitoring the growth of baby oysters (spat) planted by conservation groups and individual volunteers.

Side Trip

Head west to the Piankatank’s headwaters, a unique tidal and non-tidal stream that drains a dense cypress swamp. Dragon Run is the stream’s name, but to locals it’s simply “The Dragon,” a prime paddling/fishing destination.
Smith may have first seen the stream in the winter of 1607 while a captive of Powhatan’s war chief before he returned the following summer. The Piankatank would have valued The Dragon as a source of edible plants such as wild rice, which grows there still. And ancestors of the swamp’s stand of bald cypress trees might well have been used by the tribe to make dugout canoes. Several launch sites allow today’s paddlers to experience the mystery of these dark, cypress-stained waters where man has managed to tread lightly over the centuries. Be aware that the Dragon retains its awesome natural beauty because it is remote. Most access points by land require a trek over rugged backcountry. For information and a schedule of guided paddle trips, visit the Friends of Dragon Run.


  • Bird-watching (Piankatank Landing along the lower river and Dragon Run)
  • Fishing (chain pickerel, largemouth bass, and channel catfish in Dragon Run)
  • Hiking (trails at Piankatank Landing along the lower river and at Dragon Run)
  • Kayaking
  • Photography

Suggested Itinerary: Centers of Settlement

This tour, which can be taken by land or water, includes Gwynn’s Island, an early settlement with ties to Jamestown’s colonists and Virginia’s indigenous peoples, and Mathews, the county seat and a gateway to its rich history.

Route of Discovery

Historians can only conjecture whether John Smith visited Gwynn’s Island, a triangular wedge of land at the mouth of the Piankatank River named for the Jamestown colonist Hugh Gwynn (or Gwyn) who obtained a patent for the land in 1661. No one can verify the romantic legend that Gwynn rescued the daughter of a prominent local chief, but there’s no question that the small island has flourished. It now bustles with the comings and goings of watermen, recreational boaters, and summer visitors drawn to a place that remains quintessentially Chesapeake.

Begin to explore the island’s and other local history in Mathews, a small town whose center is a county courthouse in operation since the 1790s and the picturesque square that envelops it. At the Mathews County Visitor & Information Center, located across from the courthouse in a white clapboard building that once was a general store, you can obtain a wealth of local knowledge, maps, brochures, and an eco-tourism packet that includes the Mathews Blueways Gwynn’s Island/Milford Haven water trail and a route for touring the island by bicycle.

Getting There

Water: The 14-mile water trail (with 6.5 miles of spur routes) circles Milford Haven, the busy, bay-like waterway separating Gwynn’s Island from the mainland. The trail has three launch sites, including a public landing on the island. Sea and touring kayaks are recommended for most Blueways trails, which feature many stretches of open water.

Land: The Route 633 swing bridge provides the only vehicular access to the island.

What You’ll See

Evidence of the island’s past endures. At a wharf where steamboats and wooden ferries once docked, watermen now unload their catch of fish and crabs. A privately owned 1800s manor house, Gwynnville, graces the waterfront site where Hugh Gwynn first made his home. Meanwhile, arrowheads, pottery, and beads displayed with other artifacts in the Gwynn’s Island Museum remind visitors the island had still-earlier inhabitants than Gwynn.

Paddlers who follow the Gwynn’s Island Trail into Stutts Creek, on the western (mainland) side of Milford Haven, will pass Fitchett’s Wharf and all that remains of one of Mathews County’s noted antebellum shipyards—a pair of houses, one the shipyard owner’s former home and the other a converted wharf store.

Side Trip

Mathews is one of Virginia’s smallest counties, but it enjoyed an outsized reputation as a shipbuilding center in the 1700s and 1800s. Some 2,000 seagoing vessels were built at shipyards that dotted the county’s deepwater rivers and creeks. At least six yards thrived along the East River, a Mobjack Bay tributary whose branches fork south and west of the town of Mathews. As you paddle the Mathews Blueways Water Trails (including the 12-mile East River Trail), scan the shoreline for shallow depressions, telltale indicators of old marine railways that launched many a famous Mathews-made schooner.


  • Bicycling
  • Bird-watching (especially Sandy Point on the island’s southern tip)
  • Boatbuilding (artifacts and exhibits at Mathews Maritime Museum in Mathews)
  • Fishing (especially at the Hole in the Wall, the southern entrance to Milford Haven)
  • Kayaking
  • Swimming (Sandy Point beach)

Suggested Itinerary: Encounter the Changing Chesapeake

Bald Cypress Trees
Bald cypress trees, favored by Native Americans for their log canoes, can be seen at the headwaters of the Piankatank River. Captain John Smith reported seeing bald cypresses “three fathoms (18 feet) about the base.”

This tour, which also can be taken by land or water, follows the county’s eastern shore along Chesapeake Bay between two points of land dramatically altered since Captain John Smith first passed them.

Route of Discovery

Natural forces have reshaped the eastern (Chesapeake Bay) shoreline of Mathews County since Smith’s time, but perhaps nowhere more dramatically than the southern tip of Gwynn’s Island and New Point Comfort at the mouth of Mobjack Bay. A pair of destructive hurricanes in August 1933 cut a new channel (called the Hole in the Wall) below Gwynn’s Island and widened another between New Point Comfort peninsula and the historic lighthouse erected on what once was its tip.

This relentless interaction of land and water can be seen all along the county’s Bay shore between these two locations. Waves ripple across sugary-fine sand beaches and a web of tidal lagoons reach deep into salt marshes, forming a fertile ecosystem that sustains a variety of shorebirds, migrating waterfowl, and rare insects. The Mathews County Visitors & Information Center can direct you to nearly 40 miles of water trails, several public beaches, and two nature preserves that enable visitors to experience this magical environment firsthand.

Getting There

By Water: Two Mathews Blueways’ routes, the 15.5-mile Winter Harbor Trail and the nearly 11-mile New Point Comfort Trail (each with several additional miles of side trails) follow the Chesapeake Bay shoreline and the northern shore of Mobjack Bay. The trails have a combined eight launch sites and most paddling is in open water best suited for sea or touring kayaks.

By Land: A series of country roads and three bicycle routes that follow them will get you to the county’s beaches and waterfront nature preserves.

What You’ll See

If you’re spending only a day, be sure to visit the New Point Comfort peninsula, a favorite fishing grounds for local Indians centuries ago. Rising desolately from the peninsula’s former tip, now just a small rocky island, is the third oldest lighthouse on the Bay. Kayakers can round New Point Comfort Lighthouse by following the water trail, while an observation deck along Mobjack Bay and a nature preserve on the Chesapeake Bay shore offer equally spectacular land-based views of the octagonal-shaped icon (commissioned by Thomas Jefferson) and its rugged setting.

Birders will enjoy the coastal areas too. More than 185 avian species nest and/or migrate along the Atlantic Flyway by way of the county’s miles of unspoiled beach and salt marsh habitats. Look closely and you may see an endangered Northeastern tiger beetle here or some rather unusual winged migrants, saltwater dragonflies.

Side Trips

For a respite from Bay winds, waves, and boat wakes, the coastal water trails present paddlers with the choice of entering two protected estuaries, Winter Harbor and Horn Harbor. Its southern basin the salt marsh equivalent of a maze, Winter Harbor in particular offers a delightfully challenging network of channels and coves that meander through expanses of Spartina grasses.


  • Bicycling
  • Bird-watching (seven Bay coastal trails plus the New Point Comfort and Bethel Beach natural area preserves)
  • Fishing
  • Hiking/walking
  • Kayaking
  • Photography
  • Swimming

Local Knowledge

General stores have traditionally dispensed invaluable quantities of local news and knowledge along with their merchandise. Historic Sibley’s General Store, which dates to about 1898, continues the former role today as the home of the Mathews County Visitor & Information Center. In the heart of the town’s historic district, look for a white clapboard building with a welcoming front porch. Inside, visitors will find a one-stop wealth of local knowledge—maps, brochures, site-specific information about historic attractions, materials on suggested day trips, and trail guides for paddlers, cyclists, and birders. A resident blue crab and several small fish inhabit the center’s saltwater aquarium and a 10-minute video highlights one of the county’s most photographed landmarks, New Point Comfort Lighthouse, the third oldest of Chesapeake Bay’s surviving beacons.

The former store sells merchandise, too—folk art, hooked rugs, paintings, pottery, bird feeders, and other items handcrafted locally and on display in the center’s “Made in Mathews” Gallery.

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